$184 Cheap Flights from Billings (BIL) to Key West (EYW)

View $184 flight on Sat, Oct 25, 2025Opens in a new window

Popular airlines from Billings Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW)

Cheap Flights from Billings to Key West (BIL-EYW)

Prices were available within the past 7 days and start at $184 for one-way flights and $309 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Oct 25 - Tue, Oct 28
BIL
Billings
EYW
Key West
$309 Roundtrip, found 13 hours ago
$309
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Oct 25 from Billings to Key West, returning Tue, Oct 28, priced at $309 found 13 hours ago
American Airlines
Tue, Jan 20 - Tue, Jan 27
BIL
Billings
EYW
Key West
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jan 20 from Billings to Key West, returning Tue, Jan 27, priced at $324 found 1 day ago
Delta
Sat, Sep 20 - Fri, Sep 26
BIL
Billings
EYW
Key West
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 20 from Billings to Key West, returning Fri, Sep 26, priced at $329 found 1 day ago
American Airlines
Sat, Oct 4 - Thu, Oct 9
BIL
Billings
EYW
Key West
$343 Roundtrip, found 21 hours ago
$343
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Oct 4 from Billings to Key West, returning Thu, Oct 9, priced at $343 found 21 hours ago
Delta
Wed, Aug 13 - Thu, Aug 21
BIL
Billings
EYW
Key West
$344 Roundtrip, found 3 days ago
$344
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 13 from Billings to Key West, returning Thu, Aug 21, priced at $344 found 3 days ago
Delta
Sat, Oct 4 - Tue, Oct 7
BIL
Billings
EYW
Key West
$354 Roundtrip, found 21 hours ago
$354
Roundtrip
found 21 hours ago
Select Delta flight, departing Sat, Oct 4 from Billings to Key West, returning Tue, Oct 7, priced at $354 found 21 hours ago
American Airlines
Sun, Oct 5 - Fri, Oct 10
BIL
Billings
EYW
Key West
$372 Roundtrip, found 13 hours ago
$372
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sun, Oct 5 from Billings to Key West, returning Fri, Oct 10, priced at $372 found 13 hours ago
American Airlines
Sat, Oct 4 - Sat, Oct 11
BIL
Billings
EYW
Key West
$374 Roundtrip, found 1 day ago
$374
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 4 from Billings to Key West, returning Sat, Oct 11, priced at $374 found 1 day ago
American Airlines
Mon, Sep 22 - Fri, Sep 26
BIL
Billings
EYW
Key West
$377 Roundtrip, found 1 day ago
$377
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Sep 22 from Billings to Key West, returning Fri, Sep 26, priced at $377 found 1 day ago
United
Mon, Jan 12 - Sat, Jan 31
BIL
Billings
EYW
Key West
$545 Roundtrip, found 21 hours ago
$545
Roundtrip
found 21 hours ago
Select United flight, departing Mon, Jan 12 from Billings to Key West, returning Sat, Jan 31, priced at $545 found 21 hours ago
Flights from Billings (BIL) to Key West (EYW)
Origin airport
Logan Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$308
Distance
2088 mi

Billings to Key West Flights

The cheapest times to fly from Billings to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Billings to Key West are during the month of October. You can find some of the cheapest flights from Billings to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Billings to Key West

Sunday is one of the best days to book for cheap flights from Billings to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Billings to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Billings to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $184 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Billings to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Billings to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW) cost?
Discover the latest flight deals from BIL to EYW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from BIL to EYW?
The cheapest flights from BIL to EYW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from BIL to EYW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from BIL to EYW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW)?
Direct flights from Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from BIL to EYW?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* But this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW)?
To avoid potential delays on the Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW) route, aim to fly before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW) last-minute?
Waiting until just before your departure to book your flight from BIL to EYW often results in higher prices. While it's possible to find some last-minute offers, there's no guarantee. Keep your travel schedule open for a better chance of landing a bargain.
Is it cheaper to book a BIL to EYW flight and hotel package?
Compared with arranging flights and hotels separately, booking a BIL to EYW flight and hotel package with Expedia could result in significant savings. Better still, having everything in one place will take the stress out of planning your trip. Simply pick your flights and select from our extensive range of hotels, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Logan Intl. Airport (BIL) to Key West Intl. Airport (EYW)?
If you reserved your BIL to EYW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Explore a world of travel with Expedia

*Available to One Key members.